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Top Holiday Rentals in Chesapeake

Our top choices for Chesapeake holiday rentals

Secluded Ohio Forest Escape at Fuller's Fifty

10.0 out of 10, Exceptional, (64)
"Great cabin, secluded and as advertised. Would recommend to stay. Host was responsive and had a great time. "
The price is £77
includes taxes & fees
1 Sept - 2 Sept
Secluded Ohio Forest Escape at Fuller's Fifty

THE LUXURY CABIN IN THE WOODS

10.0 out of 10, Exceptional, (211)
"Amazing place to stay! Plenty of space for our family. we will definitely be visiting again!"
The price is £257
includes taxes & fees
26 Aug - 27 Aug
THE LUXURY CABIN IN THE WOODS

Riverside Cabin with Homemade Breakfast

9.8 out of 10, Exceptional, (39)
"Clean cabin with a great breakfast!"
The price is £120
includes taxes & fees
26 Aug - 27 Aug
Riverside Cabin with Homemade Breakfast

2BR-1B. Fire Pit With Stunning River View. Minutes From Downtown Huntington.

10.0 out of 10, Exceptional, (27)
"Great place to stay!"
The price is £146
includes taxes & fees
26 Aug - 27 Aug
2BR-1B. Fire Pit With Stunning River View. Minutes From Downtown Huntington.

This tiny cabin is a peaceful place complete with stocked pond and kayaks!

10.0 out of 10, Exceptional, (22)
"The Bunkhouse was the perfect spot for us during our visit to the area. Clean, cozy, and with all the amenities of home, with the addition of beautiful surroundings. We're already planning our next trip back!"
The price is £140
includes taxes & fees
31 Aug - 1 Sept
This tiny cabin is a peaceful place complete with stocked pond and kayaks!

"Stay Steps from Marshall - Your Home in Huntington!"

3.0 out of 10, (4)
"Relatively clean except for the floors. Can see improvements that they’ve been making. The TV in the main room does not work even though we changed the batteries in the remote never got a response from the property manager. The AC that is advertised is only a small bedroom unit in the whole apartment "
"Stay Steps from Marshall - Your Home in Huntington!"

GOLIATH RENTALS. 3-bedroom house in Rush KY. 0.1 miles from trailhead

The price is £203
includes taxes & fees
15 Sept - 16 Sept
GOLIATH RENTALS. 3-bedroom house in Rush KY. 0.1 miles from trailhead

Cozy 2-bedroom apartment located next to St. Mary's Hospital!

9.8 out of 10, Exceptional, (9)
"Great for short or long term stays. plenty of room and all amenities necessary for long stay."
The price is £163
includes taxes & fees
26 Aug - 27 Aug
Cozy 2-bedroom apartment located next to St. Mary's Hospital!

Ohio River Manor House<br>Experience the peace and quiet of a country residence!

9.8 out of 10, Exceptional, (81)
"The house and grounds are absolutely beautiful and very comfortable. Perfect for a retreat or reunion. We had a wonderful experience!"
Ohio River Manor House<br>Experience the peace and quiet of a country residence!

Hot Tub, Fire Pit: Lake-View Catlettsburg Getaway!

10.0 out of 10, Exceptional, (3)
"Place was very clean and a nice little place to enjoy with a little campfire and nice overlook of the lake "
Hot Tub, Fire Pit: Lake-View Catlettsburg Getaway!

Relaxing 2 bdrm retreat. Mountain View w hottub & ATV option 5th night free

10.0 out of 10, Exceptional, (22)
"The property great! I highly recommend!"
Relaxing 2 bdrm retreat. Mountain View w hottub & ATV option 5th night free

Cozy 2-Bdrm Cabin Fox Den- near Greenbo Lake State Park

10.0 out of 10, Exceptional, (7)
"Seemed new very clean, nice amenities. "
Cozy 2-Bdrm Cabin Fox Den- near Greenbo Lake State Park

The Park House by Nest and Bloom

10.0 out of 10, Exceptional, (9)
The Park House by Nest and Bloom

Pointer Palace

10.0 out of 10, Exceptional, (1)
"Very clean and very organized, you'll notice the attention to detail in almost every corner of the home. "
The price is £86
includes taxes & fees
26 Aug - 27 Aug
Pointer Palace

La'Chic Boutique Bungalow 3 Beds/1.5Baths

9.4 out of 10, Exceptional, (24)
"We enjoyed our stay although we had to leave for a family emergency early. Easy to get to. Clean and nice amenities. "
La'Chic Boutique Bungalow 3 Beds/1.5Baths

The Cozy Cabin 2 Bedrooms 1 Bath is the perfect romantic getaway in the country.

10.0 out of 10, Exceptional, (118)
"It was jus what we needed for our fishing trip plenty of parking and peaceful close to everything as well will stay again next year "
The price is £168
includes taxes & fees
26 Aug - 27 Aug
The Cozy Cabin 2 Bedrooms 1 Bath is the perfect romantic getaway in the country.

Hot Tub, Fire Pit: Lake-view Catlettsburg Getaway!

3.0 star property
Hot Tub, Fire Pit: Lake-view Catlettsburg Getaway!

Urban Cottage:Homey & Convenient

9.8 out of 10, Exceptional, (17)
"Very clean and plenty of room for our family to stay. "
Urban Cottage:Homey & Convenient

Corner Cottage 2 bedroom pets welcome and close to downtown

"Very quiet, clean, nice house "
The price is £194
includes taxes & fees
1 Sept - 2 Sept
Corner Cottage 2 bedroom pets welcome and close to downtown

Cozy and quiet new townhome minutes from the mall exit.

9.8 out of 10, Exceptional, (12)
"Amazing place to stay. Very clean, very spacious. Great place for the amount you pay. Will definitely stay here when we visit again."
Cozy and quiet new townhome minutes from the mall exit.
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Chesapeake Hotel Reviews

Frequently asked questions

Can I find a holiday rental in Chesapeake?

Yes, there are holiday rentals close to the most popular sights in Chesapeake, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Chesapeake has to offer?

2BR-1B. Fire Pit With Stunning River View. Minutes From Downtown Huntington.: This holiday home rental outside of Chesapeake is located on a river, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. Make the most of games in this rental home to help you unwind.

What can I see and do in Chesapeake?

Explore the area and family-friendly sights such as Camden Park Amusement Park, or get out into nature at a spot like Ritter Park. In the wider area, you’ll find Mountain Health Arena and Pullman Square.

What are holiday rentals like in Chesapeake?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Chesapeake. Holiday rentals offer amenities like WiFi and washers and dryers so your stay will be comfortable. If you're concerned about a sanitised environment, a holiday rental can provide a sense of safety away from public hotel lifts and busy reception areas while still allowing you to travel. You'll also get more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is a popular choice for a family getaway.